Director, Expansion Marketing

About The Role

As the Director of Expansion Marketing, you will lead Fresh Books’ strategy and programs that drive revenue growth from our existing customer base. You will be responsible for increasing product usage, improving cross‑sell and upsell performance, and reducing churn through targeted, marketing‑led lifecycle and engagement initiatives. You will oversee a team of Expansion Marketing Managers who build and execute programs to drive adoption across our product suite—including Payments, Payroll, core product tiers, Financial Services, and partner offerings.

This is a highly cross‑functional marketing leadership role that collaborates closely with Product, Product Marketing, Customer Success, Revenue Operations, Sales, and Data. It is an ideal role for someone with long‑term aspirations toward VP Marketing, GM, or CRO roles.

NOTE:

This role can be worked remotely from the above location.

• Lead and execute Fresh Books’ expansion strategy to grow revenue within the existing customer base by increasing product engagement, enabling tier movement, and driving adoption of add‑on offerings.
• Build and scale upsell and cross‑sell programs across multiple channels, using clear segmentation, customer insights, and value‑based messaging to drive relevant expansion.
• Design and deliver lifecycle journeys that improve product usage and retention through targeted email, in‑app messaging, and multi‑step campaigns that reinforce the value of the Fresh Books ecosystem.
• Lead, coach, and develop a high‑performing team of Expansion Marketing Managers, setting clear priorities, expectations, and accountability for results.
• Partner cross‑functionally with Product Marketing, Product, Customer Success, and Partnerships to deliver coordinated, omni‑channel expansion programs aligned to customer needs and success motions.
• Own end‑to‑end execution of expansion initiatives—planning, creative development, launch, optimization, and iteration—ensuring programs contribute meaningfully to revenue and customer outcomes.
• Own expansion analytics and reporting, using metrics such as attach rate, ARPU growth, adoption, and churn to inform decisions, optimize performance, and guide leadership discussions.

• 8+ years of experience in lifecycle marketing, expansion marketing, CRM, or revenue marketing within a SaaS organization.
• Demonstrated success driving upsell, cross‑sell, and retention programs with measurable revenue impact.
• Strong understanding of SaaS metrics including ARPU, churn, expansion rate, adoption, usage funnels, and lifecycle performance indicators.
• Experience managing and developing teams; you have led managers or senior ICs in a fast‑paced environment.
• Proven ability to work cross‑functionally and influence without authority across Product, Product Marketing, Customer Success, Sales, and Revenue Operations.
• Strong analytical skills and comfort with segmentation, experimentation, cohort analysis, and performance reporting.
• Exceptional execution discipline, with the ability to manage multiple programs simultaneously and deliver strong outcomes.
• Excellent communication and storytelling skills with a customer‑focused mindset.
• A high degree of agency; you have a bias for action and strong follow‑through.

• Experience running your own business or direct experience working with small and micro businesses with a deep understanding of their operational needs.

At Fresh Books, we approach each individual's compensation with a promise of fair market value and internal equity commensurate with experience and specific skill set. The total annual compensation for this role ranges from CA $145,000 to CA $182,000, which may include participation in our incentive programs. Additionally, this position offers an equity grant and immediate enrollment in Fresh Books' comprehensive benefits program.

• 🩺 Comprehensive health and wellness benefits. Generous time off including a flexible vacation plan, a retirement savings program or pension plan matched to your local office, stock options for every full‑time employee, parental leave and new parent support, annual…